Lindane

Lindane
Ball-and-stick model of the lindane molecule
Systematic (IUPAC) name
(1r,2R,3S,4r,5R,6S)-1,2,3,4,5,6-hexachlorocyclohexane
Clinical data
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • C
Legal status
  • Production and agricultural use is banned the 169 countries that parties to the Stockholm Convention, but pharmaceutical use is allowed until 2015.[1]
Routes of
administration
Topical
Pharmacokinetic data
Protein binding 91%
Metabolism Hepatic cytochrome P-450 oxygenase system
Biological half-life 18 hours
Identifiers
CAS Registry Number  Y
ATC code P03 QP53 QS02
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C6H6Cl6
Molecular mass 290.83 g/mol
 Y   

Lindane, also known as gamma-hexachlorocyclohexane, (γ-HCH), gammaxene, Gammallin and sometimes incorrectly called hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.[3][4]

Lindane is a neurotoxin that interferes with GABA neurotransmitter function by interacting with the GABAA receptor-chloride channel complex at the picrotoxin binding site. In humans, lindane affects the nervous system, liver and kidneys, and may be a carcinogen.[5][6] It is unclear whether lindane is an endocrine disruptor.[7][8][9]

The scabies.[11]

Contents

  • History and use 1
    • United States 1.1
      • Pharmaceutical uses 1.1.1
      • Morton Grove lawsuit 1.1.2
  • Human health effects 2
    • Cancer risk 2.1
    • Endometriosis risk 2.2
    • Adverse reactions to lindane 2.3
  • Environmental contamination 3
    • Isomers 3.1
  • See also 4
  • References 5
  • External links 6

History and use

The chemical was originally synthesised in 1825 by Faraday. It is named after the Dutch chemist Teunis van der Linden (1884–1965), the first to isolate and describe γ-Hexachlorcyclohexane in 1912. Its pesticidal action was discovered only in 1942, after which lindane production, by Imperial Chemical Industries Ltd (ICI), and use started up in the United Kingdom. It has been used to treat food crops and to forestry products, as a seed treatment, a soil treatment, and to treat livestock and pets. It has also been used as pharmaceutical treatment for lice and scabies, formulated as a shampoo or lotion.[12][13][14] It is estimated that between 1950 and 2000, around 600,000 tonnes of lindane were produced globally, and the vast majority of which was used in agriculture. It has been manufactured by several countries, including the United States, China, Brazil, and several European countries, but as of 2007 only India and possibly Russia are still producing it.[12]

By November 2006, the use of lindane had been banned in 52 countries and restricted in 33 others. Seventeen countries, including the US and Canada, allowed either limited agricultural or pharmaceutical use.[12] In 2009, an international ban on the use of lindane in agriculture was implemented under the